Jimmy makes his first appearance in Grade 8 in the third episode, Family Politics, in which his girlfriend, Ashley Kerwin, is running for, school president. Jimmy is seen with his best friend, Spinner Mason, as they tease Emma Nelson and Manny Santos. Jimmy also bribes J.T. Yorke, along with Spinner and Ashley. When Ashley wins the election, he congratulates her and walks her home.
Jimmy is unintentionally rude to Sean Cameron, who is repeating the 7th grade. At the school dance, Jimmy Invites him to an 8th graders-only after party in which he took it the wrong way, and nearly beat him up until Emma asked to dance with Sean, saving them both.
Coming up to his and Ashley's 8-month anniversary in The Mating Game, Jimmy is pressured to have sex with her by Spinner at the same time Paige is doing the same to Ashley. Also, in class they are studying Romeo and Juliet, with Jimmy and Paige playing the main roles. Ashley and Jimmy make plans to have sex, but at the sex talk with Dr. Sally, Ashley becomes worried and backs out. Jimmy assures her that he won't leave her for Paige and they spend the evening blowing up their condoms, content with their romantic yet non-sexual relationship.
In Coming of Age, Jimmy begins spending too much time with her. Jimmy has developed a strong bond with Toby and is at her house for dinner almost every night. Ashley is ready to dump him but he instead dumps her because he doesn't want her pity, but when he ends up alone on his 14th birthday, thanks to his workaholic parents, he leaves Ashley a distraught message saying that her family is all that he has. Ashley decides to stay with him.
In Basketball Diaries, Jimmy is trying out for the basketball team, but he is having trouble with English and is jealous of Sean's skill. Jimmy shows some potential, but is still struggling compared to Sean, and when it comes down to it, he's not the star. When he finds out that he has an English test on the same day as basketball tryouts, he chooses English, and passes the test. However, he makes a mistake by convincing Spinner to give him Ritalin for the tryouts to improve his game. However, Jimmy is rough on the other players (mainly Sean) and the coach only sees him as a bully, thus turning him away. Spinner also moons everyone without his medication, and both boys receive detention.
In Friday Night, Spinner and Jimmy get into trouble once again when they disrespect their strict English teacher, Ms. Kwan. After they leave Friday detention, they decide to prank her during her adult classes and egg her car. This causes Ms. Kwan to have a breakdown and the boys are surprised. The next day, they are talking about it in class when Ashley says that it was mean, yet Hazel is supportive of the two until they learn that her husband is very sick and so she was under emotional and financial stress. The boys are nicer to her in the future.
After Sean finishes his exams in Under Pressure, he is on edge and when Jimmy makes a few comments about it, they organize a fight. Emma and Ashley try to convince their boyfriends to call it off, but their rivalry knows no bounds. When Emma tries to split it up physically, she ends up getting pushed to the ground, which stops the fight, and leaves them both remorseful about what they did.
In Jagged Little Pill, Ashley's parents are out of town, and both she and Toby are allowed to have one friend over, but Ashley cheats and invites Paige, Terri and Hazel. Toby ends up inviting other friends as well such as J.T. and Sean. When Ashley consumes an ecstasy tablet, she invites Jimmy and Spinner, who could tell she was high and Emma, Manny and Liberty also arrive. After dancing with everyone and making an idiot of herself, Ashley makes out with Sean in front of Jimmy and then dumps him, telling him everything she thought of their relationship which hurt him deeply. Ashley feels horrible the next day, but Jimmy doesn't want to talk to her and so their romance is over.
In Karma Chameleon, Ashley was accepted back into the popular clique and Jimmy begins flirting with her. However, when word gets out that Ashley accepted a date from Sean, Jimmy, as he thought they might get back together and disowns her, calling her a "slut".
Jimmy's rivalry continued with Sean to the point where he did not attend a boys-only get together at Craig's house in Drive.
In Shout (1), when Spinner is ready to date Paige, Jimmy helps him out.
In Shout (2), Ashley helps Paige through her rape and begins to win her old friends back.
When Spinner is embarrassed because of his body odor problems in Hot for Teacher, he asks Jimmy to be truthful to him from now on and they end up being truthful to others as well, such as when Jimmy says that Ashley's poems are trying too hard to be poetic (but she later thanked him). Jimmy and Spinner got into a big fight about the truth, which resulted in Jimmy revealing that his parents didn't like Spinner, and Spinner revealing that Jimmy's at his house all the time. They make up in the end and agree not to be truthful at everything.
In Message in a Bottle, Jimmy is holding a party and invites Ashley. He gets insecure when Sean turns up and begins drinking his parents' alcohol, but they make a truce and Jimmy decides to rekindle things with Ashley.
In Dressed In Black, they both clearly had feelings for each other but were just awkward. Both parties are overjoyed but Ashley senses something isn't right when he doesn't understand one of her songs and keeps an old photo of her in his locker. Ashley gives him a new one, but he doesn't use it. Their class is studying The Taming of the Shrew, and both Ashley and Craig agree that it is wrong to "tame" someone and begin working together on the project. Craig and Ashley have more in common and he is more comfortable with her goth looks than Jimmy. Ashley ditches her goth look but decides it is wrong to change herself and asks Jimmy which photo he prefers of her. Jimmy picks the grade 8 Ashley and they break up, but not on bad terms.
In Fight for Your Right, Spinner is also very jealous of Jimmy's wealth and in class, when they are surfing the net they come across a shopping site. Jimmy can afford things, but Spinner can't and the latter ends up stealing Jimmy's MP3 Player. Jimmy discovers this, and Spinner returns it. He tries to apologize, but Jimmy distrusts him and this causes a rift.
At the end of the year in Tears Are Not Enough (2), Jimmy became closer to Hazel and even though they weren't dating, they did enter the luau together against Paige and Spinner at the end of year dance. They got quite competitive, and different obstacles got in the way of each winning. They all ended up loosing to Ashley and Craig.
In the beginning of the year in Father Figure (1), Spinner wants to get Paige a more desirable locker and gets Jimmy to agree to swap lockers with her- on the condition that in class he admits to being spineless and being controlled by his girlfriend. Jimmy humiliated the couple, but they made up in the end.
In U Got the Look, Jimmy also joins Craig's band, Downtown Sasquatch, and is frustrated when Joey becomes too controlling over it, along with all of the other members. Craig is forced to tell Joey the band's feelings.
In Pride (2), Jimmy is also very supportive of Marco when he comes out, and comforts him when he is gay bashed. Spinner has problems with it, however. When he writes 'Marco is a fag" on a wall in the boys' bathroom, Jimmy is disgusted and asks Spinner if he's going to add something about Jimmy being black. Later, he organizes a sleepover with Marco and Spinner, where Marco saves Spinner from choking on a piece of cheese, which helps them later come to terms with the former's sexuality. Jimmy also performs in a Battle of the Bands competition with Downtown Sasquatch.
In Accidents Will Happen (1), Toby was hurt that he wasn't Jimmy's friend anymore and that J.T. had been ditching him to spend time with Jimmy's clique. When Jimmy got a bad grade in math, he asked Toby if he could hack into the grade system and change it. However, when Toby hacks into the system in the Library, accidentally changes the grade to "8888%". When he tries to fix it, Mr. Raditch catches Toby and asks him who he was trying to help. Toby rats Jimmy out and they both receive Saturday detention. Jimmy approaches Toby and calls him "100% fake".
Jimmy performs in a Battle of the Bands competition with Downtown Sasquatch in Rock and Roll High School.
However, in Saturday detention in Take On Me, everything changes. The attendees are Sean, Ellie, Toby and Hazel as well as Jimmy and everyone has to reveal why they were there in a game of truth or dare. However, Hazel declines her truth (she later admits she was surfing porn) and Jimmy dares her to kiss Toby, which she does. They are all bonding when Mr. Raditch separates them. However, they all end up regrouping and take a trip through the school, ending up on the rooftop. On the rooftop, Jimmy gives Hazel a necklace and kisses her for kissing Toby. They then start dating. Mr. Raditch then spots Toby so they all rush back inside. However, there is evidence of an escape and Toby takes the blame, which Jimmy admires and thanks him for. Just as Ellie is getting ready to take a group photo, her tape recorder falls out and it reveals that she was double crossing Sean, which the others are disgusted by. On Monday, all of the attendees are friends except for Ellie. Jimmy and Hazel say hello to Toby in the hall.At the end of the year in The Power of Love, Jimmy's relationship is going very well with Hazel and he wants to make the end of year dance special for her. However, Jimmy ends up wearing a sari and their very Western-styled limo driver is arrested, so they arrive to the dance in a police car. The place they made reservations to have dinner at is no good, since Spinner and Paige ran off without paying a few weeks earlier.
Just when Jimmy is enjoying himself with Hazel, the school almost burns down and they have to continue the dance in the parking lot. Jimmy is down and Hazel asks what's wrong, to which he relays his feelings. Hazel says that if he wants to make her happy, all he is has to do is dance with her and for the first time, he is really happy.
Season 4When Rick returns to the school in Mercy Street, Jimmy bullies him like everyone else because he was violent towards his friend, Terri MacGregor. They corner him at The Dot but he is defended by Emma.
When Heather Sinclair becomes ill and cannot be on the Degrassi team for the academic challenge 'Whack Your Brain' in Time Stands Still (1), Jimmy is asked to compete. Jimmy is at first cold towards Rick, but then changes his ways, warms up to him, and finally believes that the bullying has gone too far. When Jimmy defends Rick in front of Alex, Jay and Spinner they decide to play a prank on him. Meanwhile, Rick has told his mother that he, Emma, Toby and Jimmy have become inseparable.
When Rick answers the tiebreaker question correctly in Time Stands Still (2), he is excited as it is being filmed and Emma gives him the trophy. However, yellow paint and feathers are dropped on him, leaving everyone to laugh at him.
Humiliated, Rick briefly goes home, but returns to school with a gun to kill Emma and considers killing Paige, until she unexpectedly apologizes to him, unknowingly saving her own life. Rick then overhears Spinner and Jay falsely imply that Jimmy was behind the prank, knowing Rick was there thinking that he would tell Mr. Raditch or fight Jimmy, Instead, Rick went to find Jimmy and the latter comforted him. He said that he had his back, when Rick said "you stabbed me in the back" and shot Jimmy in the back, leaving him paralyzed from the waist down. Both Hazel and Spinner are shocked about this.
Jimmy was well supported in the aftermath of the shooting, especially by Hazel, Craig and Marco. Hazel was a little too cautious though, Craig showed up often discussing his love life with Ashley, and Jimmy really wanted to see a Kid Elrick concert, so Craig and Marco helped him escape the hospital to see it in Secret (2). Since he had to stay longer at the hospital because they were not done fixing the house. When they returned, Jimmy's dad found out and was very angry, but calmed down once Jimmy explained the situation.
When Jimmy returns to school in Eye of the Tiger, everyone is thrilled, except for Spinner, who is feeling guilty. Jimmy is angry that he never visited him. When Spinner confesses his part in the shooting, he is disowned because of what he did. So a drunk Spinner shows up univinted at Craig's to Apologize to Jimmy in which he gets no response from him and Craig tells him to go home. When Spinner gets into his car to drive away, Jimmy stops him, and tells him he can't be mad at someone he doesn't care about. Spinner confesses to Principal Ms. Hatzilakos about what he and Jay did (he leaves Alex presumably for not being in involved in Jimmy getting crippled despite the fact she poured the paint & feathers on Rick), and is expelled. Jimmy is also seen at the prom, and Hazel tries to make it special for him. When Paige begins complaining about everything, Hazel stands up to her.
In Venus (1), Jimmy is seen at Craig's surprise 17th birthday party at the Dot.
In Death of a Disco Dancer, Jimmy also began coaching the younger basketball team, but had a problem with Derek Haig, who wouldn't listen to him and ridiculed him. Derek said that a cripple couldn't teach him anything, unaware of what happened with Rick. When Jimmy proved him wrong by beating him in a one on one penalty shoot out, he realized he deserved more respect.
In Foolin', Jimmy tries to thwart Darcy and Spinner's new relationship by wheeling into The Dot and making a smart remark, but Darcy defends him.
In I Still Haven't Found What I'm Looking For, Jimmy is caught between wheelchair basketball tryouts and drawing. Ellie discovers his talent and takes him to an art exhibition which he enjoys, but causes him to miss tryouts. His father is angry, so he gets him another shock but Jimmy turns it down. Hazel is also mad and concerned for him and they have a fight. However, Hazel talks with him and says he's still the same Jimmy, but he disagrees and says that he's different and can't explain, but Hazel asks him to try and he agrees.
When Jimmy helped the painting of the wall mural at Degrassi in Redemption Song, Hazel helped as well. He promised that he would paint a picture of her face on it, but he instead painted Ellie's. Hazel confronted him over it, and Jimmy said that even though he loved Hazel, he admired Ellie. Hazel then dumped him and Jimmy realized that he had begun to fall for Ellie.
When Ashley returns from London in High Fidelity (2), he confides in her that he likes Ellie and Ashley believes that she likes him back, when she implies she has a crush. She tries to push them together, but it becomes apparent that Ellie likes Craig instead. Ellie tells Jimmy that she loves him as a friend, and he runs off. The next day, he thanks Ashley and says that no on wants to be with a guy in a wheelchair, but Ashley stops him and kisses him, rekindling their middle school romance. Jimmy also learns that because he's had so much time off school for physio therapy etc., that he doesn't have enough credits to graduate and must stay back one extra year. Jimmy briefly blames Spinner, after his kiss with Ashley, he decides to forgive Spinner.
After Ashley's return from England, Jimmy and Ashley saw old love in each other. However, after attempting to take a step forward with sexual relations in Can't Hardly Wait, Jimmy realized that his physical damage has unfortunately made it hard for him to get an erection. Jimmy goes to physical therapy at lunch time, and as he is taking Spinner's advice about relaxing, he notices that he gets an erection. Excited about this, he goes to see Spinner and talks about his new discovery. Spinner tells him to tell Ashley, who is conveniently coming approaching them in the hallway. He tells Ashley to come over to his house that night, saying that his parents aren't going to be home, telling her that it can finally work between them. He brings her to his house, and she starts the seduction. After 20 minutes, he notices that he is attracted to her, but he doesn't get an erection. Furious and embarrassed, he tells her that there is nothing she can do, and kicks her out of his house.
Jimmy apologizes to Ashley in the hall the next day, and she said she wasn't mad that he couldn't get hard, but because he kicked her out when she threw herself at him. Jimmy apologizes again, and after some talking, they both decide to seek medical help to help Jimmy with his problem.
That following night, Jimmy tries out the Viagra, and Ashley gives him a massage to calm him down, so that the Viagra will work. He tells her that it's useless to try, that it won't work.
Jimmy tells Ashley it's over, because he cannot satisfy her, saying to come over to his house and get her stuff. That night, Jimmy lets Ashley in, and they mutually agree they do not want to break up. He said that he wants to make this work, and Ashley said they will be able to, that he is all the man she has ever wanted.
Also, in a Season 6 deleted scene, Jimmy was shown searching the Internet on the anatomy of the penis, due to his erectile dysfunction. The website showed how males achieve an erection in their penis by giving a diagram from flaccid to erect state.
In Working for the Weekend, Jimmy decides that Spinner needs to get out of the funk he's in, and start having some fun. He goes over to Ellie and Marco's house after school. After Paige compliments Spinner's new shirt, Spinner gets that idea that he and Jimmy should start selling the shirts with Jimmy's designs. He plans the whole thing out in hopes of avoiding his future as a clown. At lunch, he starts to pitch different stores names to Jimmy. After begging him, Jimmy finally decides to go for it. They set up shop on the side of a busy road. Several people buy their shirts, and they end up selling out. As the two pass a 'For Lease' sign on the ledge of a window on an empty building, Spinner gets the idea that they should open up a shop. With the money he saved up from working at the Dot and the money Jimmy has in his trust fund, it was made possible. Spinner starts doubling the prices of everything in hopes of gaining a bigger profit. One night, two men enter the shop when Jimmy was there by himself. When Spinner enters, the two men are in different spots. One guy is holding the box with their money in it and the other guy is grabbing onto Jimmy. Spinner nails the guy grabbing Jimmy to the wall, allowing the other guy to escape with the money. When the police arrive, Jimmy decides not to reopen the shop even if the money is found. Spinner says Jimmy's lucky that he has so much talent, but Jimmy reminds Spinner of the way he pinned the thief to the wall, and adds that he could make a great cop one day.
When Craig returned to Toronto in October in What's It Feel Like to Be a Ghost? (1), Jimmy came to Marco's house to welcome him home and listened to him sing his new song, Drowning.
During October 2006, J.T. Yorke is stabbed and killed by a Lakehurst thug in Rock This Town. Jimmy is present at J.T.'s funeral and memorial at Degrassi in The Bitterest Pill. When Ellie was interviewing the students on their opinions about J.T. and if he was a target by the Lakehurst students, Jimmy states that he felt that J.T.'s killer was a ticking time bomb, and if it wasn't J.T., it would have been someone else that would have been eventually killed. Ellie's information would later be submitted to her article at The Core.
Season 7When Craig's album Of Two Minds finally came out in It's Tricky, and Ashley found out that he didn't credit her for one of the songs used. Jimmy was happy that he was mentioned in the shout-outs, but the album inspired Ashley to go back into music. Ashley wanted Jimmy to follow her on her dreams, so he wrote a rap to perform with her. She decided to write Jimmy out of the song, and to go on stage alone. When she performed, the crowd dog-sold for her to play a song by Craig. Jimmy saved her by going onto the stage with his rap. Ashley thought that people only saw her as Craig's ex-sidekick, and she didn't want to be Jimmy's, but she still encouraged him to pursue a music career. Griffin, Ellie's new roommate, heard the track and asked Jimmy to perform at a show. Jimmy still wanted Ashley there with him, but she stepped aside so Jimmy could get the spotlight. Griffin showed their work to a producer, and asked them both to make a demo. Jimmy was excited about his opportunity and asked Ashley to manage it. Ashley ended up deleting Jimmy's rap and sent the producer just her song instead. When Jimmy found out about this he called her his biggest disappointment.
When Spinner told Jimmy that he felt pain in his testicles in Death or Glory (1), Jimmy told him he should have it checked out. After Spinner visited a doctor, he told Jimmy the doctor thought he may have testicular cancer. Jimmy was shocked, but told him it will be fine and that no one gets cancer at 18. After Spinner went on a date with Jane, she playfully poked him in the balls with a pool stick, which caused him extreme pain and he later found out he had developed testicular cancer, but that they caught it very early. Eventually, after nearly having a third fight with Johnny DiMarco in Death or Glory (2), Spinner went through with the operation.
In We Got the Beat, Jimmy meets a girl named Trina at his physical therapy class. He discovers that she became disabled from a fall while rock climbing, but she tries to adjust to her conditions, encouraging Jimmy to do the same. In time, Jimmy grows to like her and realizes he likes Trina more than Ashley. After he breaks up with her, Jimmy and Trina begin to date, and he later proposes to her. Trina inspires Jimmy to get stem cell surgery.
After recently being accepted to go into Hudson University to study law in Broken Wings, Jimmy decides to use his grant money to pay for the surgery. However, his father doesn't approve and tells him to wait a few years for research into stem cells to advance. But after catching his father having an affair, Jimmy questions himself for trying to live up to a man who didn't have any standards himself. After a confrontation with his father, Jimmy decides to go through with the surgery and at dinner that night, he tells his parents he wants to go to Amsterdam with Trina and have the surgery done as soon as possible, but doesn't tell his mother about his father's infidelity.
In Lost in Love (1), Jimmy returns to Toronto with Trina to celebrate Spinner's acceptance into police school, unaware that Spinner lied to Jane Vaughn about getting accepted when he was actually rejected. Jimmy states that his treatment was progressing well, and his and Trina's conditions were continuing to improve. When Jane got angry with Spinner for lying, Jimmy consoled him and helped him through it. He also revealed to Spinner that he is going to propose to Trina. In a deleted scene, it shows Jimmy in a limo with Trina. He proposes to her with a ring, and she says yes. This is Jimmy's final appearance.
- He is one of many present and former Degrassi students who don't go by their full name. The others being:
- Zig (Zigmund)
- Drew (Andrew)
- Becky (Rebecca)
- Cam (Campbell)
- Eli (Elijah)
- Fitz (Mark)
- K.C. (Kirk Cameron)
- Sav (Savtaj)
- Dave (David)
- Dallas (Michael)
- Jake (Jacob)
- Mo (Mohammed)
- Ellie (Eleanor)
- Tiny (Deon)
- Frankie (Francesca)
- J.T. (James Tiberius)
- Manny (Manuella)
- Holly J. (Holly Jeanette)
- Jimmy (James)
- Jay (Jason)
- Alex (Alexandra)
- Toby (Tobias)
- Wheels (Derek)
- Joey (Joseph)
- Alli Bhandari (Allia)
- Spinner (Gavin)
- Danny (Daniel)
- Jack (Jacqueline)
- Blue (Bradley)
- Rick (Richard)
- Luke (Lucas)
- B.L.T. (Bryant Lester Thomas)
- Johnny (Jonathan)
- Spike (Christine)
- Snake (Archie)
- L.D. (Lorraine Delacorte)
- Bronco (Basil)
- He had a conflict with Sean Cameron, but they are both currently on good terms.
- Two people involved in Jimmy's shooting, Rick and Spinner, were also shot. Rick was shot in the same episode, Time Stands Still (2), and Spinner in Danger Zone.
- Jimmy and Hazel were the second-longest lasting Degrassi couple in history, lasting nearly two years.
- Both Jimmy and Spinner graduated a year late because of conflicts with their credits, in the aftermath of the school shooting.
- Jimmy is one of two characters to have their actor mentioned on the show after they left. The other is Shenae Grimes.
- Jimmy was one of six characters in the Degrassi Franchise to have to use a wheelchair, the other five being Maya Goldberg, Nadia Yamir, Trina, Mr. Ehl, and Margaret Matlin.
- Jimmy is one of seven characters to get shot. The other six were Claude Tanner, Rick Murray, Sean Cameron, Spinner Mason, Adam Torres, and Damon Carter.
- Jimmy and J.T. both have the same birth name "James."
- He is the second out of eight to intentionally harm someone else's car. He egged Ms. Kwan's car. The other seven are:
- Spinner, who started egging Ms. Kwan's car before him.
- Paige, who crashed Spinner's car into Dean Walton's.
- Rick Murray, who spray-painted an "X" on Spinner's and Jay's car doors.
- Mark "Fitz" Fitzgerald, who broke a hood ornament off of Eli's hearse.
- K.C. keyed Coach Armstrong's car.
- Katie, who egged Bianca's car, before breaking off the right side-view mirror.
- Zig, who dumped garbage on Madame Jean-Aux's car.
- Jimmy, Katie, and Liberty all share the same line "You're dead to me."
- Jimmy is one of several characters to be held back. The others are Rick Munro, Joey, Sean, Rick Murray (before his death), Spinner, Fiona, Tori, Drew, Imogen, Dallas, Jonah, and Esme.
- In Jane Says (1), it is revealed that Spinner and Jimmy had been friends since before they were four.
- He had a neighbor named Osama.
- Jimmy was one of five athletes to be involved with drugs. The other four are Toby, Riley, Drew and Katie.
- Jimmy was the second character that felt mortified when purchasing condoms from a drugstore. The first was Joey.
- Judging as all of his attempts have sex have failed, it can be inferred that Jimmy is still a virgin.
- Jimmy's portrayer was mentioned twice: The first time in Degrassi Takes Manhattan and the second time in I Want It That Way (2).
- Jimmy was good friends with Toby in Season 1, because he was dating his stepsister Ashley, and was constantly at their house.
- It was revealed in Season 1 that Jimmy's parents are rarely around.
- Jimmy bears similarities to former Degrassi student Archie Simpson and future Degrassi students Mike Dallas.
- He and Archie were both the "voice of reason" to their less responsible best friend, Spinner and Joey, respectively. Additionally, following a major tragedy, both stopped speaking to a best friend because they felt that person was responsible (Snake stopped speaking to Wheels after he drove drunk, crashed and wound up hurting Lucy and killing a child; Jimmy stopped speaking to Spinner because of his role in the school shooting). Both were athletic, Archie was a great swimmer and Jimmy was a great basketball player.
- Like Dallas, Jimmy was a popular athlete. Dallas played for the Toronto Ice Hounds and Jimmy was the MVP of the basketball team. Both got cut from their team, but for very different reasons (Dallas was cut from the Ice Hounds because of the coach making room for new talent. He was later drafted by a Japanese hockey team; Jimmy had to stop playing for the Panthers because of his paralysis. He later started playing again, but as a coach).
- Jimmy was the first person shown having an uncomplicated/good relationship with the parent of the person that he/she was dating in this series:
- Jimmy had a good relationship with Ashley's parents.
- Holly J. Sinclair had a good relationship with Declan's mother.
- Dave had a good relationship with Alli's parents.
- Jenna had a good relationship with K.C.'s mother.
- Fiona had a good relationship with Imogen's mother.
- Bianca had a good relationship with Drew's mother.
- Tiny has a good relationship with Shay's parents.
- Jimmy's father was having an affair with his co-worker. It was not revealed when the affair started or if it stopped, or if his mother ever found out.
- Despite being paralyzed from the waist down in Season 4, he remained a part of the basketball team as an assistant coach until he graduated in Season 7.
- Jimmy and Ashley were the first couple to be shown on DTNG.
- Jimmy and Ashley had the first break-up in DTNG.
- Jimmy and Ashley were the first couple of DTNG to think about having sex.
- Jimmy had the first on-screen kiss of DTNG with Paige.
- It was for an English assignment in Kwan's class of Romeo and Juliet.
- Jimmy never liked Rick Murray, even before he started abusing Terri MacGregor.
- Jimmy and Spinner are the first characters in the series to be shown graduating a year later.
- After this, having a senior stay back an extra year became a repeating theme on the show.
- Jimmy was Marco's first male friend to be accepting of his sexuality.
- He stood up to Spinner for Marco.
- Jimmy and Ashley are the first and only couple to make more than one attempt to have sex and fail each time.
- Jimmy was the first character on DTNG to be praised for his athletic ability.
- Jimmy was the first character on DTNG to be cheated on.
- Jimmy was the first character to escape from the hospital with a friend's help and come back without getting caught by doctors or nurses. He escaped with the help of Marco and Craig. The second one was Clare who escaped with Drew's help.
- Jimmy wanted to attend NYU with Ashley to practice law.
- Jimmy is the third of four characters to catch their parent having an affair. The other three are Caitlin Ryan, Emma, and Miles.
- Jimmy is the only character that didn't tell their parent that the other parent was having an affair.
- As revealed in Goin' Down the Road (1), Craig trusted Jimmy enough to tell him that he was bipolar.
- In It's Tricky, it was revealed that Craig mentioned Jimmy in the acknowledgements of his album Of Two Minds.
- Ashley's mother Kate Kerwin was very fond of Jimmy. She often invited him over for dinner and was very upset when he was shot in Time Stands Still (2).
- Jimmy is the third of three characters to blackmail another character. He blackmailed his father to get stem cell surgery. The first character was Arthur who blackmailed his sister into letting his friend copy her school papers. The second character was Joey who blackmailed Dwayne for $314.
- Jimmy is a fan of Kid Elrick and DJ Mad Bullets.
- Like Melanie Brodie, he was allergic to flowers.
- (To Ashley): "What was that all about?" (first line) - Family Politics
- (To Spinner, referring to Spinner and Jane): "Just make sure that no matter what, you're going to be there for each other." (final line) - Lost in Love (1)
- (To Spinner, referring to Marco): "So what are you gonna write next? Something about me being black?" - Pride (2)
- (To Rick, referring to his gun.): "Is that real?" - Time Stands Still (2)
- (To Spinner, referring to exams) "When in doubt, pick 'C'." - If This Is It
- Limo Driver: "James Brooks?"
Jimmy: "Yeah. But, there must be some mistake!" (Jimmy referring to limo). - The Power of Love
- Jimmy: "You better go, Del Rossi."
Marco: "Fine, but pizza and Spin-"
Jimmy: "Always a bad combo?" - Pride (2)
- (To Spinner): "You have a brain?"
Spinner (sarcastically): "Ha! Ha!" - Basketball Diaries
- "Manny Santos, my how you've grown." - Venus (2)
- Ellie: "Okay, I cannot believe Friendship Club brainwashed Spinner!"
Jimmy: "There's not much brain to wash." - I Against I
- (To Spinner): "And then he shot me." - Eye Of The Tiger
- (To J.T.): "Don't be all up in my fries, Dawg." - It's Raining Men
- (To Spinner): "Your friend's gay, stop hating and just deal." - Against All Odds
- (To Spinner): "C'mon I'm not gonna let you stay home all night writing another sad-ass, 'wa wa I'm gonna kill myself' poem." - Working for the Weekend
- "Finish high school... WALK outta here..."
- "Yeah, sure. I'll run over their feet with my wheelchair." - What's It Feel Like to Be a Ghost? (2)
- Jimmy: "A homie is a player, that is all. So why'd you have to go and kick his..."
Spinner: "Ball and chain, ain't that your name? 'Cause you a playa hater and that's a shame."
Jimmy: "And chicks like you ain't worth too much, so shut up girl,"
Spinner & Jimmy: "AND MAKE MY LUNCH.... YEAH!!" - Rock & Roll High School
- (To Ashley): "Don't talk to me, you slut..." - Karma Chameleon
- Jimmy: "You want the truth?"
Jimmy: "YOU CAN'T HANDLE THE TRUTH!" - Hot for Teacher
- "Alex, a heart! Try to find one." - Queen of Hearts
- "Well, je suis up for skipping." - Queen of Hearts
- (To Ashley, after they break up in Coming of Age): "What are you, deaf? GO!"
- "Spin, you move like a wounded Polar Bear. Sorry, buddy." - Girls Just Wanna Have Fun
- "You come to my house, and you steal my parents' booze?" - Message in a Bottle
- (To Craig): "Look, the music you have us playing is lame. Wedding bands are lame, ergo; YOU'RE LAME!" - Weddings, Parties, Anything
- (To Ellie in The Bitterest Pill): "The thing is, life is random. Sometime's it's tragic, and totally messed up. But there's one thing that makes all the drama and tears worthwhile. If you're lucky enough to find someone you love, who loves you back, it's a gift."
- (To Marco): "It's okay. It's okay, I'm here. I'm here and not going anywhere, okay?" - Pride (2)
- (To Marco and Paige in Lost in Degrassi): "It hasn't even been a year...ass."
- "I need to see something other than you two and these ugly-ass walls." - to Craig and Marco in Secret (2).
- "I was shot in the back running from a trivia nerd covered in yellow paint and feathers."
- Jimmy: "That's just weak, grow up!"
Alex: "Oooh, Ricky found a friend."
Jimmy: "Give it a rest. It's boring. - Time Stands Still (1)
- (To Ashely) "Wherever I go, You're coming with me." - It's Tricky
- (To Spinner when playing basketball) "And that is why you don't try to beat the master at his own game." - It's Tricky
- Ellie: "I'm such a stupid klutz."
Jimmy: "You're not a klutz at all. You're perfect." - Man in the Mirror
- Jimmy: "Ellie, hi."
Ellie: "What's up?"
Jimmy: "You look great. I mean you always look great, but tonight you look great!"
Ellie: "Oh hey I was just wondering. How do I look? Could it maybe be great?"
(Jimmy laughs nervously)
Jimmy: "Um, look you've become one of my best friends, right and you've opened my eyes to a lot of things. I wanted to know if maybe we could talk about taking it to the next level..."
(Ellie doesn't say anything)
Jimmy: "But you don't."
Ellie: "Jimmy, I'm sorry...I--"
Jimmy: "Don’t be. It’s not completely unexpected. I’m gonna go, okay?" - High Fidelity (2)
- (Craig shows Jimmy and Marco his science exam in which he got an A+)
Jimmy: "A! That's my man."
Marco: "Wow. That's amazing, buddy."
Craig: "Yeah, my dad actually did something worthwhile for me. He was a good study partner."
Jimmy: "Look we're really sorry to hear about your dad, man."
Marco: "Yeah. So you okay?"
Craig: "Guys, I'm fine. Hey, I'm the lucky one. My dad died. I, I walked away with a scratch."
Marco: "I thought you weren't in the car..."
Craig: "Friday night, we're like speeding down the highway, my dad's mad and he won't slow down. Ahead there's a rig. I see it, my dad doesn't and we hit...hard."
(Jimmy and Marco are shocked. Craig laughs)
Craig: "Guys, I was at Joey's when it happened! I had you going though." - Tears Are Not Enough (2)
- Craig: "I got news! Big news! You ready?"
(Craig takes his trousers off)
Jimmy: "What?! No. Hold on!"
Craig: "First wedding I ever went to was my mom's to Joey. Spike and Simpson's was number two. Ashley's dad makes three. See I want to get my practice down, you know? Get things right before my own wedding."
Jimmy: "Okay, you got time for that."
Craig: "I asked Ashley and she said yes."
Jimmy: "You're actually getting married?"
Craig: "Congratulations! Anytime..."
Jimmy: "You're sixteen. Don't you want to wait for I don't know, graduation? Maybe an occupation?"
(Craig is not listening and is trying to button his cuffs)
Craig: "Could you do this up? Please?"
Jimmy: "Are you drunk? Are you high? Or are you just out of your mind?"
Craig: "I love her!"
Jimmy: "Okay, that still doesn't explain what's up with you or this insane idea!"
Craig: "Maybe you should just think about it and try to understand. I don't know, be happy for me!" - Voices Carry (2)
- Ashley: I could never get tired of London. You know, but I got tired of missing home. I’ve had some schools there, but couldn’t find anything quite like this.
Jimmy: Yeah, I guess it’s kind of hard to find a school with such a unique combo of shootings and gonorrhea outbreaks. - High Fidelity (2)
- Main article: Jimmy-Ashley Relationship
- Ashley Kerwin
- First Relationship:
- Second Relationship:
- Third Relationship:
- Fourth Relationship:
- Main article: Jimmy-Hazel Relationship
- Hazel Aden
- Main article: Jimmy-Trina Relationship
- Main article: Ashley-Jimmy-Sean Love Triangle
- Ashley Kerwin and Sean Cameron
- Main article: Jimmy-Hazel-Ellie Love Triangle
- Hazel Aden and Ellie Nash
- Main article: Jimmy-Ellie-Craig Love Triangle
- Ellie Nash and Craig Manning
Alex • Alli • Anya • Ashley • Blue • Bruce • Caitlin • Chantay • Clare • Connor • Craig • Damian • Danny • Darcy • Dave • Declan • Derek • Ellie • Emma • Fiona • Hatzilakos • Hazel • Holly J. • J.T. • Jane • Jay • Jenna • Jimmy • Joey • Johnny • K.C. • Kelly • Leia • Liberty • Manny • Marco • Mia • Paige • Peter • Raditch • Riley • Sav • Sean • Snake • Spike • Spinner • Terri • Toby